A coastal landscape with a beach, ocean waves, and a sunset sky.

Find Hotels with a Pool in Wainscott, NY

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Check availability on Wainscott Hotels with a Pool

Tonight
Sep 3 - Sep 4
Tomorrow
Sep 4 - Sep 5
This weekend
Sep 4 - Sep 6
Next weekend
Sep 11 - Sep 13

Our top choices for Wainscott hotels with a pool

1. The Sagaponack

The Sagaponack
Wainscott
  • Take a summer dip in the seasonal outdoor pool with loungers for relaxing in the Hamptons sun.
$304 nightly
$340 total
Oct 4 - Oct 5
Total with taxes and fees
The Sagaponack

2. Wainscott Woods Retreat

Wainscott Woods Retreat
Wainscott
  • Seasonal outdoor pool at oceanfront hotel offers garden views and nearby vineyard tours for summer retreats.
$715 nightly
$816 total
Sep 9 - Sep 10
Total with taxes and fees
Wainscott Woods Retreat

3. A Room At The Beach

A Room At The Beach
Bridgehampton
  • Soak up sunshine and serene vibes at this Hamptons motel with a stylish outdoor pool.
$329 nightly
$376 total
Oct 4 - Oct 5
Total with taxes and fees
A Room At The Beach

4. East Hampton House Resort

East Hampton House Resort
East Hampton North
  • Seasonal outdoor pool creates a refreshing escape at this hotel, with tennis courts and gardens adding to the resort atmosphere.
$271 nightly
$310 total
Sep 28 - Sep 29
Total with taxes and fees
East Hampton House Resort

5. Ocean Vista Resort

Ocean Vista Resort
Amagansett
  • Oceanside sanctuary provides splendid private beach access and indoor pool oasis.
$127 nightly
$145 total
Oct 1 - Oct 2
Total with taxes and fees
Ocean Vista Resort

6. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
  • Swim into serenity at this charming Sag Harbor retreat with a seasonal outdoor pool and balcony views.
$324 nightly
$370 total
Oct 4 - Oct 5
Total with taxes and fees
Sag Harbor Inn

7. Hamlet Inn

Hamlet Inn
Southampton
  • Serene seasonal pool retreat with private beach access just 2 miles away offers the perfect summer escape on Long Island.
$146 nightly
$164 total
Sep 27 - Sep 28
Total with taxes and fees
Hamlet Inn

8. Journey East Hampton

Journey East Hampton
East Hampton North
  • Seasonal poolside splendor at East Hampton hotel with complimentary bikes and garden views.
$341 nightly
$390 total
Oct 4 - Oct 5
Total with taxes and fees
Journey East Hampton

9. The Bentley Hotel Southampton

The Bentley Hotel Southampton
Southampton
  • Dive into the pristine oasis of the seasonal outdoor pool, complete with umbrellas and loungers for ultimate relaxation.
$166 nightly
$190 total
Sep 27 - Sep 28
Total with taxes and fees
The Bentley Hotel Southampton

10. Sea Crest Resort

Sea Crest Resort
Amagansett
  • Coastal serenity awaits at this oceanfront hotel with an inviting pool and comfortable loungers for relaxation.
$185 nightly
$211 total
Sep 28 - Sep 29
Total with taxes and fees
Sea Crest Resort
View all properties

Choose what matters most at hotels with a pool in Wainscott

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Wainscott Hotel Reviews

 Hampton's Vacation Inn

Hampton's Vacation Inn

10/10 Excellent
"Loved our stay! The staff was very helpful. Would definitely stay again!"
Diane 1-night trip
Posted 7 hours ago
Hampton's Vacation Inn
The Hampton Maid

The Hampton Maid

10/10 Excellent
"wonderful hotel."
SABINA 1-night trip
Posted 12 hours ago
The Hampton Maid
Ocean Surf Resort

Ocean Surf Resort

10/10 Excellent
"Stutaff was kind and the room was clean. It was very nice to be close to the sea. I had a good time. Thank you"
naoko 1-night trip
Posted 13 hours ago
Ocean Surf Resort
Kenny's Tipperary Inn

Kenny's Tipperary Inn

8/10 Good
"Nice hotel and very clean, and the staff were very courteous and helpful. Beach is walking distance right down the road. Perfect location if you're looking for something by the beach."
Demetra 4-night trip
Posted 15 hours ago
Kenny's Tipperary Inn
Faraway Sag Harbor

Faraway Sag Harbor

8/10 Good
"Faraway has been renovated Beautifully. The food has improved since Baron's Cove. The pool would benefit improving service and perhaps combining the food / drinks servers and pool attendants. In addition since we have been guests of the older Hotel, Baron's Cove for 16 years it would have been meaningful to have the new staff welcome guests and perhaps give a priority rate or welcome massage etc."
Claudia 3-night trip
Posted 17 hours ago
Faraway Sag Harbor
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"Great beachfront property! Spa is amazing!"
Daniel 1-night trip
Posted 1 day ago
Gurney's Montauk Resort & Seawater Spa
Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"This was a beautiful property on the water. We went to celebrate a birthday and it was the perfect location. The bedrooms were large and had high end toiletries. The restaurants on the property were delicious and had excellent service. It's also pretty centrally located and was only a few minutes from the downtown area. Highly recommend this property."
Arabella 1-night trip
Posted 2 days ago
Montauk Yacht Club

Frequently asked questions

How much does a hotel with outdoor pool in Wainscott cost?
Enjoy staying in a hotel in Wainscott with an outdoor pool. You can find a great deal from $145 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
Are there hotels in Wainscott with outdoor pool cabanas or loungers?
The Sagaponack is a charming 3-star hotel in Wainscott that offers a delightful outdoor pool experience. Guests rave about the inviting pool area, featuring comfortable sun loungers and shaded umbrellas, great for lounging on a sunny day. With a review rating of 8.8, visitors appreciate the hotel's friendly staff and the nice decor that adds to the overall appeal.Beyond the pool, The Sagaponack also provides complimentary toiletries and free WiFi, ensuring a convenient stay for families. Plus, self-parking is available at no additional cost, making it easy to explore the beautiful surroundings of Wainscott.
Is it cheaper to book flights and a Wainscott hotel with a pool as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Wainscott for you.

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